Essential oil variation within and between Stachys inflata Benth. and Stachys lavandulifolia Vahl. p

J. Bio. Env. Sci. 2016 Journal of Biodiversity and Environmental Sciences (JBES) ISSN: 2220-6663 (Print) 2222-3045 (Online) Vol. 8, No. 2, p. 240-248, 2016 http://www.innspub.net RESEARCH PAPER

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Essential oil variation within and between Stachys inflata Benth. and Stachys lavandulifolia Vahl. populations from Iran Seyed Mehdi Shahgolzari*, Afagh Yavari Department of Biology, Payame Noor University, Tehran, Iran Article published on February 28, 2016 Key words: Essential oils, GC–MS, Stachys inflata, Stachys lavandulifolia.

Abstract Although several species of Stachys possess characteristic essential oils, only a few published studies have described within and between populations of their volatile constituents. The aim of the present study was to evaluate the chemical composition of essential oils from two chemically unexplored Stachys species, Stachys lavandulifolia and Stachys inflata. Populations of these species were collected from Touyserkan, Hamedan province west of Iran. The essential oils of the dried flowering aerial parts of two species were isolated by hydrodistillation and analysed by means of GC and GC–MS. In this survey, 12 populations of both species were studied. Then data obtained were analyzed by Pc-ord software. 64 oil components were identified. 6, 10, 14trimethyl-2-pentadecanone, Dibutylphthalate, isobutyl phthalate, spathulenol, trans-caryophyllene and αcopaene was observed in all populations of two species. δ-3-carene, Mytenal and α-thujene only in S. lavandulifolia and E-Citral (Geranial), n-docosane, neryl acetate, Nerylphenylacetate, Z-citral (Neral) only in S. inflata was observed. No similarity was observed between the chemical profile of essential oils obtained from S. lavandulifolia and S. inflata. The results of the present study indicated that essential oil components of S. lavandulifolia and S. inflata could be varied within and between populations. *Corresponding

Author: Seyed Mehdi Shahgolzari  Mehdi.shahgolzari@gmail.com

240 | Shahgolzari and Yavari

J. Bio. Env. Sci. 2016 Introduction

were collected in different habitats from Touyserkan,

The genus Stachys, one of the largest genera of the

Hamedan province west of Iran (May 2013).

Labiatae (Lamiaceae) family with around 300 taxa, is widely distributed across the world from tropical to

Plant material and essential oil preparation

subtropical regions (Piozzi and Bruno, 2009 &, 2011).

The

The genus is geographically wide spread and found

lavandulifolia and S. inflata were collected at full

mostly in the Mediterranean, South Western Asia,

flowering stage. A voucher specimen (code numbers

North and South America and South Africa. The

of

native species are, however, absent in New Zealand

deposited at the Herbarium of Biology Department,

and

Stachys

Payame Noor University, Touyserkan, Hamedan,

lavandulifolia Vahl. and Stachys inflata Benth. type

Iran. The air-dried materials were finely ground, then

of Stachys genus (Lamiaceae family) has been widely

subjected to hydro-distillation for 3 hours with water

studied based on its essential oil and therapeutic

as solvent, using a Clevenger apparatus according to

characteristics over the recent decades. In Previous

the standard procedures. The oils were stored at 4 oC

studies

for further analyses.

Australia

on

S.

(Bhattacharjee,

lavandulifolia

1980).

(Ghannadi

and

aerial

parts

populations

of

different

1001-1012)

of

populations

population

S.

was

Alemdoost, 1996; Alamdoost, 1996; Feizbaksh et al., 2003; Javidnia et al., 2004; Hajhashemi et al., 2006;

Gas chromatography–mass spectrometry (GC–MS)

Meshkatalsadat et al., 2007; Amiri et al., 2009; Asadi

Volatile components were identified by GC-MS using

et al., 2010; Nadaf et al., 2011; Sadrmomtaz et al.,

a Finnigan TRACE GC-MS (Thermo Quest Finnigan

2011; Pirbalouti et al., 2011; Jafarzadeh et al., 2012;

Co., USA) equipped with a DB-1 capillary column (60

Soleimani- Meimand et al., 2013; Aghaei et al., 2013;

m × 0.25 mm × 25µm). Helium (flow rate, 1.1

Pirbalouti and Mohammadi, 2013; Meimand et al.,

ml/min) was used as the carrier gas, and injection

2013; Tundis et al., 2015) and S. inflata (Garjani et

volumes were 0.2 µl. The oven temperature was

al., 2004; Sajjadi and Somae, 2004; Norouzi-Arasi et

raised from 60 ºC to 250 ºC at a rate of 5 ºC /min,

al., 2005; Ebrahimabadi et al., 2009; Nabizahedasl et

held at 250 ºC for 5 min; transfer line temperature

al., 2010; Rustaiyan et al., 2011; Omidbaigi et al.,

was 250 ºC. Split ratio was 100. The quadruple mass

2013; Yavari and Shahgolzari, 2013; Shahbazi et al.,

spectrometer was scanned over the 40-460 amu with

2014; Talebi et al., 2014) different compounds of oil

an ionizing voltage of 70 eV and the injector

were reported. The differences in qualitative and

temperatures were kept at 250 ºC. The constituents of

quantitative compositions of the essential oils were

the oil were identified by calculation of their retention

found on both specific and population levels.

indices under programmed temperature conditions

According to existing references and information,

for n-alkanes (C8-C24) and the oil on a DB-1 column

individuals of this species are present in many

under

stations with different ecological conditions. We are

individual compounds was made by comparison of

becoming increasingly aware that an individual

their mass spectra with those of the internal reference

cannot be considered out of the context of its

mass spectra library or with authentic compounds

environment. With regard to the wide distribution of

and confirmed by comparison of their retention

S. lavandulifolia and S. inflata in Iran we wanted to

indices with authentic compounds or with those

know if there is essential oil diversity within and

reported in the literature (Adams, 2001).

the

same

conditions.

Identification

of

between populations of these species in studied area.

Chemical variability Material and methods

Analytical data for cluster analysis were treated by

Location

means of the Pcord-4 with group linkage method

12 populations of wild S. lavandulifolia and S. inflata

(nearest neighbor).

241 | Shahgolzari and Yavari

J. Bio. Env. Sci. 2016 Results and discussion

moderate antibacterial activity of ß-caryophyllene and

The essential oil compositions of the Stachys genus

germacrene D were reported. Germacrenes were

have been well documented in the literature, but not

produced as antimicrobial and insecticidal agents

for all the species have been described in detail. The

from Stachys species (Omura et al., 2006; Goren et

main components of the essential oil of the species

al., 2011). α- pinene, ß-caryophyllene, linalool oxide

were observed to be germacrene D, caryophyllenes,

and caryophyllene oxide were tested against several

cadinene,

bacterial strains.

spathuleneol

and

caryophyllene.

The

Table 1. Essential oil composition of S. lavandulifolia and S. inflata populations from studied area (%).

Compounds

1,8-Cineol 4a-α,7-α,7a-α-Nepetalactone 4-Terpineol 6,10,14-trimethyl-2pentadecanone 6,9-Guaiadiene ar-Curcumine bicyclo Elemene bicyclogermacrene Caryophyllene oxide Cembrene cis-sabinene hydrate cis-sesquisabinene hydrate cis-ß-bisabolene cryptone cumin aldehyde δ-3-carene Dibutylphthalate E-Citral( Geranial) E-Nerolidol E-ß-Farnesene E-ß-Ionone Germacrene D humulene epoxide Intermedeol isobutyl phthalate isospathulenol limonene linalool Mytenal n-docosane neryl acetate Nerylphenylacetate n-tetradecane P-Cymene pirollene pristane sabinene Sesquisabinene spathulenol terpinolene trans- verbenol trans-caryophyllene trans-pinocarveol trans-α-bergamotene Viridiflorol Z-citral (Neral) α-bisabolol α-Cadinol α-campholenal

IR 1038 1365 1186 1848

Populations of S.lavandulifolia Khangormaz Serkan P1 P2 P3 P4 1.47 1.57 0.23 0.62 0 0.06 0.07 0.09 0.12 0.03 0 0.05 1.05 0.26 2 1.87

Sarabi P5 0.45 0.03 0 0.47

1454 1492 1350 1517 1608 1964 1072 1565 1551 1194 1248 1017 1969 1272 1569 1460 1496 1501 1633 1684 1874 1658 1035 1100 1205 2204 1381 2013 1401 1029 1103 1709 978 1466 1600 1049 1154 1441 1150 1447 1617 1244 1696 1674

0 0 0 0 16.4 0 0.09 0 0 0.04 0.32 0 4.72 0 0 0 0 0.22 0.13 1.63 18.4 0 0 0.77 0.16 0 0 0 0 0 0 0.63 0 1.78 0.94 0 0.62 14.4 0 0.3 0 0 0 0

1132 0.39

P6 0.4 0 0 1.4

Population of S.inflata Khangormaz Serkan Average P7 P8 P9 P10 0.79 0 0 0 0.2 0.04 0 0.06 0 0.2 0.04 0 0 0 0 1.17 0.54 1.34 5 1.3

Sarabi P11 0.2 0.1 0 0.9

P12 5 0 0.6 0.3

Average 0.9 0.07 0.11 1.6

0.06 0.03 0.43 13.17 3.3 0.25 0.51 0.04 0.27 0 0.27 0.63 1.45 0 0.42 2.3 0.16 8.21 0.22 0.08 3.24 0.87 14.31 0.09 0.18 0 0 0 0.28 0.1 0.1 0.22 0.86 0 10.28 0.93 0.64 14.58 0.16 0.47 0.3 0 0.03 0.17

0.04 0.13 0.02 0.4 16.3 0.18 0.01 0.14 0 0 0.11 0 1.02 0 1.44 1.56 0.53 0.13 0.7 1.17 4.12 2.8 0.13 0.12 0.04 0 0 0 0.17 0 0.04 1.16 0 0 50.7 0.09 0.12 7.98 0.31 0.42 0.68 0 0.07 1

0.13 0.02 0.38 1.96 4.26 0.37 0.05 0.21 0.09 0 0.39 0.07 0.8 0 1.18 4.76 0.2 2.74 0.17 0 0.75 2.01 0.31 0.22 0.21 0 0 0 0.77 0.02 0.22 0.72 0.07 0 40 1.03 2.19 17.7 0.14 1.41 0.41 0 0.02 0.67

0 0.02 0.26 6.84 5.19 0.74 0.02 0.11 0.17 0 0.06 0 4.1 0 0.72 3.67 0.29 4.94 0.15 0 0.72 1.84 2.36 0.06 0.11 0 0 0 0.46 0 0.1 0.99 0.07 0 26.2 0.55 0.55 25 0.25 0.93 0.48 0 0.1 0.24

0.1 0.2 0.1 0.8 0 0.8 0 0.2 0 0.2 0.2 0 2.1 0 0.8 2.2 0.3 0 0 0.7 16 2.4 0.6 0 0 0 0 0 0.8 0.1 0.1 0.6 0 0 52 0.1 0.2 7.8 0.1 0.4 0.9 0 0.1 0

0.06 0.07 0.2 3.87 7.57 0.38 0.12 0.12 0.1 0.03 0.23 0.12 2.36 0 0.75 2.42 0.24 2.71 0.24 0.6 7.22 1.65 2.95 0.22 0.12 0 0 0 0.41 0.03 0.09 0.72 0.17 0.3 30 0.45 0.72 14.6 0.16 0.65 0.47 0 0.05 0.35

0 1.3 0 0 0 0 0 0 0 0 0 0 15.1 3.95 0.18 0 0 0.56 0 0 8.45 0 1.15 0 0 0.25 0.48 6.64 0 0 0 0 0 0.19 41.6 0 0 4.15 0 0 0 2.86 0 1.6

0 0.08 0 0.05 5.84 0.7 0 0 0.05 0 0 0 34.66 0 0.08 0.22 0.08 0.27 0.25 0.91 24.68 0.82 0.24 0 0 0 0 0 0.03 0 0 1.91 0 0 20.15 0.09 0.06 2.15 0 0.07 1.03 0 0.21 0.69

0 0 0 5 18 0 0 0 0 0 0 0 5 0 0 1 2 13 0 4 1 2 0 0 0 0 0 0 1 0 0 1 0 0 21 1 0 7 0 0 3 0 0 0

0.2 0.5 0.2 6.9 4.3 0.4 0 0 0.2 0.2 0.5 0 2.6 0 0 0.3 2.1 6.5 0.7 0 1.1 6 0 0 0 0 0 0 0.3 0 0 1.3 0 0 47 0 0.8 0.9 0 1.1 4.4 0 0 4.5

0.1 0.1 0.6 18 2.6 0.1 0.1 0.1 0.2 0.1 0.2 0.1 5.9 0 0.2 0.9 1 23 0.3 0 0.8 1.7 2.4 0.1 0 0 0 0 0.9 0.1 0 0.7 0.2 0 19 0.1 0.3 3.6 0.2 0.6 1.4 0 0 1

0 6.1 0 0 6.1 0 0.1 0 0 0 0 0 2.5 26 0.7 0 0 0.1 0 0 0.1 0 5.2 0 0 0 0.9 0.2 0 0.6 0.1 0 0.3 0.4 9.5 0 0 4 0 0.1 0 20 0 1.7

0.09 1.34 0.19 4.94 6.18 0.27 0.03 0.02 0.1 0.05 0.16 0 10.9 5.07 0.2 0.33 0.9 7.1 0.22 0.88 5.97 1.72 1.5 0.02 0 0.05 0.23 1.13 0.41 0.13 0.02 0.85 0.08 0.1 26.3 0.17 0.21 3.59 0.05 0.39 1.64 3.78 0.04 1.56

0.43

0.1

0.91

0.46

0.2

0.42

0

0

0

0

0.2

0

0.05

242 | Shahgolzari and Yavari

J. Bio. Env. Sci. 2016 α-copaene α-humulene α-phellandrene α-pinene α-Terpineol α-thujene ß-bourbonene ß-elemene ß-Myrcene ß-phellandrene ß-Pinene γ-Terpinene δ-Cadinene Number of compounds Total oil

1392 1474 1010 940 1197 931 1403 1405 991 1036 985 1063 1538 ----------

0.38 0.38 0 0.29 0.33 0 0 0.05 0 0 0 0.11 0 27 66.1

1.23 0.14 0.28 1.5 0.27 0.17 0.45 0.34 9.39 0 1.06 0.24 2.2 50 99.23

1.14 0.09 0 0 0.16 0 0.16 0.16 0.06 0 0 0 0.21 44 98.2

2.1 0.37 0 0.1 0.68 0.02 0.83 0.44 0.91 2.21 0.14 0.1 1.49 53 99.5

0.76 0.39 0.03 0.07 0.32 0 0.29 0.47 2.49 1.93 0.31 0.07 1.4 49 98.2

2.4 0.2 0 0.1 0.1 0 0.6 0.4 0.1 0.4 0.2 0.1 1.1 42 98

1.34 0.26 0.06 0.35 0.31 0.03 0.38 0.31 2.15 0.75 0.28 0.11 1.07 -------93.3

0.23 0 0 0 0 0 0.07 0 0 0 0 0 0.74 19 90.1

0.07 0 0 0.01 0.11 0 0.02 0.12 0.04 0 0.01 0.04 0.4 29 97.54

2 0 0 0 0 0 2 0 0 0 0 0 2 19 98

1 0.8 0 0 0 0 0.9 0 0 0 0 0 2 31 99

1.4 0.8 0.1 3 0 0 0.1 0.1 0.3 1.4 2.5 0.2 2 49 99

1.1 0 0 0.2 1.2 0 0 0 0 0 0 0 0.5 26 94

The essential oil composition of Stachys species

According to previous studies, various components of

mainly consists of sesquiterpenes and oxygenated

essential oil on this both species have been reported.

sesquiterpenes. Moreover, the monoterpenes such as

This shows that the volatile oil composition of those,

α-pinene, ß-pinene, phellandrene and carvacrol were

in Iran is extremely variable (Naghibi et al., 2005;

also extracted from Stachys species. S. lavandulifolia

Semnani et al., 2006; Arasi et al., 2006; Goudarzi et

and S. inflata are medical plants that can be a

al., 2011).

potential source of monoterpenes and sesquiterpenes.

Fig. 1. Dendrogram representing similarity relationship between S. lavandulifolia and S. inflata species based on essential oil constituents.

The essential oil compositions of our samples for S.

based on their essential oil composition (namely

lavandulifolia and S. inflata are shown in Table 1.

analysis of the two species together). 6, 10, 14-

According to the GC mass analysis a total of 62

trimethyl-2-pentadecanone,

compounds were identified in S. lavandulifolia and S.

isobutyl phthalate, spathulenol, trans-caryophyllene

inflata together. The dendrogram (Fig. 1) represents

and α-copaene was observed in all populations of

graphically the relationships between the populations

both species. Based on these results, the essential oil

of S. lavandulifolia and S. inflata and the groups,

variation patterns in Stachys species exhibited more

243 | Shahgolzari and Yavari

Dibutylphthalate,

0.88 0.34 0.01 0.53 0.22 0 0.51 0.04 0.06 0.25 0.43 0.03 1.27 -----96.2

J. Bio. Env. Sci. 2016 diversity. The highest oil compounds in two Stachys

lavandulifolia and E-Citral( Geranial), n-docosane,

species were Spathulenol. The highest percentage was

neryl acetate, Nerylphenylacetate, Z-citral (Neral)

recorded in population 3 (50.7%) and the lowest in

only in S. inflata was observed. No similarity was

population 1 (0.94%). To assess the use of essential

observed between the chemical profile of essential oils

oil constituents in identifying taxonomic relationships

obtained from S. lavandulifolia and S. inflata. Figure

between species, multivariate analysis by nearest

1 shows the separation between populations. On the

neighbor complete linkage cluster analysis were

other hand, the two species from Stachys were

initially performed with oil constituent. Therefore,

clustered in 2 groups, and were clearly different from

two groups of populations were identified. δ-3-

the others.

carene,

Mytenal

and

Îą-thujene

only

in

S.

Fig. 2. Dendrogram representing similarity relationship between S. lavandulifolia populations based on essential oil constituents.

Fig. 3. Dendrogram representing similarity relationship between S. inflata populations based on essential oil constituents.

244 | Shahgolzari and Yavari

J. Bio. Env. Sci. 2016 The dendrogram (Fig. 2, 3) represents graphically the

within and between the species was determined by

relationships within the populations and the groups

using essential oil analysis could prove useful for the

of both species, separately. The major components of

classification of two species in relation with locality of

S. lavandulifolia according to average essential oil in

species. Oil constituents in the Stachys species show

populations

(3.87%),

excessive diversity in Iran and these compounds

(7.57%) isobutyl phthalate

strongly differentiated them. The application of single

(7.22%), spathulenol (30%) and trans-caryophyllene

linkage clustering produced two large clusters within

(14.6%). The highest total essential oil was recorded

the population, it is therefore concluded that essential

in populations 4 (99.5%) and the lowest ratio was

oil

obtained in populations 1 (66.1%).

identification

Caryophyllene

were oxide

bicyclogermacrene

could

be

useful and

markers

classification.

in

population

These

results

suggested that essential oils data could clearly The numbers of identified compounds in the essential

separate different populations of two species from

oil of the 6 populations ranged from 27 to 53. Total

each other. Essential oil analyses of S. lavandulifolia

percentages of identified compounds however, varied

and S. inflata species found in Touyserkan, Hamedan

from 66.1% to 99.5%. The average value of the totally

province west of Iran have revealed high chemical

identified compounds was 93.3% (Table 1). The major

polymorphism in within and between populations,

components of S. inflata according to average

possibly related to edaphic, genetic and ecological

essential oil in populations were Z-citral (Neral)

influences.

(3.78%), bicyclogermacrene (4.94%), Caryophyllene oxide (6.18%) isobutyl phthalate (5.97%), spathulenol

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